I don't encourage watching Decade, but I usually don't recommend skipping it entirely.

DiEnd.... ONORE-DIEND!

Oooooh...I am NOT seeing a lot of love for Decade. Hmm. I never see hate for Gokaiger, but I'm seeing no love for Decade. Wow. :lol

There are three differences in Gokaiger vs, Decade-

1- Emotion.
2- Plot, story, characters
3- No Luka Milfy.

Gokaiger also had an ending that wasn't confusing and open ended.. and confusing.

Ah, yes...God, I love Gokaiger...

Anyway, what season would be best for me to start after OOO? It'll be over soon enough, considering I just started episode 31...Isn't the last new combo in the next episode?

Decade *dramatic pause* sucks...
It has no proper history, the AU Rider worlds are rather hit or miss, and a lot of people hate Tsukasa, plus it has no ending so to speak.

It's a good way to learn more about the previous riders, and watching it intermitently can be fun. But overall it has more flaws than strenghts.

Don't let us stop you from watching it though, but only do so if you are really interested, don't do it expecting a great show and don't do it for Super Hero Taisen because that's even worse.

W aka Double!
It's OOO predecessor and the beggining of waht we call the "Neo-Heisei" era, he also teamed up with OOO in various movies so you need his show to watch the movies.
And overall W is simply awesome it's one of the best regarded Rider shows of recent time.

Are you loving OOO craziness and somewhat randomness at moments? Id suggest Den-O. Actually, I recommend Den-O anyway. But if you want a good series, story, and characters, Id say W.

Hmm...Okay. W is next after OOO. I'll probably save Den-O, which I believe is a Time Travel themed show...anyway, I'll probably reward myself with Den-O after Decade if I really hate it.

Honestly? I would head over towards Fourze. It's the next series in line and follows the spirit of OOO. Alot of the stories have alot of feels, and it's funny. But also serious when it has to be.

Plus that means you get to watch the Fourze/OOO movie with Nadeshiko and Super TaToBa. And who could say no to that?